Ethane

In the laboratory, ethane may be conveniently prepared by carbon dioxide and methyl radicals, and the highly reactive methyl radicals combine to produce ethane:

e⁻

CH₃• + •CH₃ → C₂H₆

Another method, the oxidation of peroxides, is conceptually similar.

The chemistry of ethane also involves chiefly free radical halogenation. This reaction proceeds through the propagation of the ethyl radical:

C₂H₅• + C₂H₅Cl + Cl•

Cl• + C₂H₆ → C₂H₅• + HCl

Because halogenated ethanes can undergo further free radical halogenation, this process results in a mixture of several halogenated products. In the chemical industry, more selective chemical reactions are used for the production of any particular two-carbon halocarbon.

Combustion

The complete combustion of ethane releases 1561 kJ/mol, or 51.9 kJ/g, of heat, and produces chemical equation

2 C₂H₆ + 7 CO₂ + 6 H₂O + 3122 kJ/mol

Combustion occurs by a complex series of free-radical reactions. Computer simulations of the peroxide into ethoxy and hydroxyl radicals.

C₂H₅• + O₂ → C₂H₅OO•

C₂H₅OO• + HR → C₂H₅OOH + •R

C₂H₅OOH → C₂H₅O• + •OH

The principal carbon-containing products of incomplete ethane combustion are single-carbon compounds such as formaldehyde. One important route by which the carbon-carbon bond in ethane is broken to yield these single-carbon products is the decomposition of the ethoxy radical into a methyl radical and formaldehyde, which can in turn undergo further oxidation.

C₂H₅O• → CH₃• + CH₂O

Some minor products in the incomplete combustion of ethane include ethanol. At higher temperatures, especially in the range 600–900 °C, ethylene is a significant product. It arises via reactions like

C₂H₅• + O₂ → C₂H₄ + •OOH

Similar reactions (although with species other than oxygen as the hydrogen abstractor) are involved in the production of ethylene from ethane in steam cracking.

Production

After methane, ethane is the second-largest component of natural gas. Natural gas from different gas fields varies in ethane content from less than 1% to over 6% by volume. Prior to the 1960s, ethane and larger molecules were typically not separated from the methane component of natural gas, but simply burnt along with the methane as a fuel. Today, however, ethane is an important petrochemical feedstock, and it is separated from the other components of natural gas in most well-developed gas fields. Ethane can also be separated from petroleum gas, a mixture of gaseous hydrocarbons that arises as a byproduct of petroleum refining. Economics of building and running processing plants can change, however. If the relative value of sending the unprocessed natural gas to a consumer exceeds the value of extracting ethane, then the plant may not be run. This can cause operational issues managing the changing quality of the gas in downstream systems.[1]

Ethane is most efficiently separated from methane by liquefying it at cryogenic temperatures. Various refrigeration strategies exist: the most economical process presently in wide use employs turboexpansion, and can recover over 90% of the ethane in natural gas. In this process, chilled gas expands through a turbine; as it expands, its temperature drops to about -100 °C. At this low temperature, gaseous methane can be separated from the liquefied ethane and heavier hydrocarbons by distillation. Further distillation then separates ethane from the propane and heavier hydrocarbons.

Uses

The chief use of ethane is in the chemical industry (usually uses a catalyst to boost up the reaction), in the production of ethylene by steam cracking. When diluted with steam and briefly heated to very high temperatures (900 °C or more), heavy hydrocarbons break down into lighter hydrocarbons, and aromatic hydrocarbons.

Experimentally, ethane is under investigation as a feedstock for other commodity chemicals. Oxidative chlorination of ethane has long appeared to be a potentially more economical route to INEOS operates a 1000 t/a ethane-to-vinyl chloride pilot plant at Wilhemshaven in Germany.

Similarly, the Saudi Arabian firm SABIC has announced construction of a 30,000 t/a plant to produce acetic acid by ethane oxidation at Yanbu. This economic viability of this process may rely on the low cost of ethane near Saudi oil fields, and it may not be competitive with methanol carbonylation elsewhere in the world.

Ethane can be used as a refrigerant in cryogenic refrigeration systems. On a much smaller scale, in scientific research, liquid ethane is used to ice crystals can do.

Health and safety

At room temperature, ethane is a flammable gas. When mixed with air at 3.0% – 12.5% by volume, it forms an explosive mixture.

Some additional precautions are necessary where ethane is stored as a cryogenic liquid. Direct contact with liquid ethane can result in severe frostbite. In addition, the vapors evaporating from liquid ethane are, until they warm to room temperature, heavier than air and can creep along the ground or gather in low places, and if they encounter an ignition source, can flash back to the body of ethane from which they evaporated.

Containers recently emptied of ethane may contain insufficient carcinogen.

Atmospheric and extraterrestrial ethane

Ethane occurs as a trace gas in the fossil fuels. Although ethane is a greenhouse gas, it is much less abundant than methane and also less efficient relative to mass. It has also been detected as a trace component in the atmospheres of all four giant planets, and in the atmosphere of Saturn's moon Titan.

Atmospheric ethane results from the Sun's hydrogen atom. When two methyl radicals recombine, the result is ethane:

CH₄ → CH₃• + •H

CH₃• + •CH₃ → C₂H₆

In the case of Titan, it was once widely hypothesized that ethane produced in this fashion rained back onto the moon's surface, and over time had accumulated into hydrocarbon seas or oceans covering much of the moon's surface. Infrared telescopic observations cast significant doubt on this hypothesis, and the Huygens probe, which landed on Titan in 2005, failed to observe any surface liquids, although it did photograph features that could be presently dry drainage channels. The Cassini probe though has found evidence of lakes at the poles of Titan, where it is hypothesised, that it is cold enough for methane and ethane to liquify.

In 1996, ethane was detected in Comet Hyakutake, and it has since been detected in some other comets. The existence of ethane in these distant solar system bodies may implicate ethane as a primordial component of the solar nebula from which the sun and planets are believed to have formed.

References

Michael Faraday (1834). Experimental researches in electricity: Seventh series. Philosophical Transactions, 124:77–122.
Hermann Kolbe, Edward Frankland (1849). On the products of the action of potassium on cyanide of ethyl. Journal of the Chemical Society, 1:60–74.
Edward Frankland (1850). On the isolation of the organic radicals. Journal of the Chemical Society, 2:263–296.
Hermann Kolbe (1850). Researches on the electrolysis of organic compounds. Journal of the Chemical Society, 2:157–184.
Carl Schorlemmer (1864). Annalen der Chimie, 132:234.
Michael J. Mumma et al. (1996). Detection of Abundant Ethane and Methane, Along with Carbon Monoxide and Water, in Comet C/1996 B2 Hyakutake: Evidence for Interstellar Origin. Science, 272:1310–1314.

References

^ Trace gases

Computational Chemistry Wiki
Molview from bluerhinos.co.uk See Ethane in 3D
Market-Driven Evolution of Gas Processing Technologies for NGLs
Extra information on Ethane

v • d • e Octane ( C₈H₁₈ ) • Nonane ( C₉H₂₀ ) • Decane ( C₁₀H₂₂ ) • Undecane ( C₁₁H₂₄ ) • Dodecane ( C₁₂H₂₆ )

Alkanes

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